Chapter 1 - The Plan

"I don't know what to do. I can't just go alone. Literally everyone will be coupled up. Everyone. I can't be the one single person surrounded by those judgy bitches in one of the most romantic countries in the world," Sansa bemoaned.

"So then don't go on the trip," Arya said with a shrug, as if the answer was so clear.

"It's Italy, Arya. You know it has always been my dream to go there."

"Then go. Ignore those judgy bitches. Who cares what they think? Their opinions don't matter."

"Okay, it's like you and I didn't even go to the same school. Of course their opinions matter. Most of them have very important connections through their families."

Arya shook her head. "That's just stupid. You don't need them, their opinions, or their so-called connections."

"Well, Joffrey's parents are paying for the trip for everyone. All I have to pay for is the flight and food. They're covering hotels, tours, and transportation throughout Italy. So I do need that."

"Yikes. What are the Baratheons trying to cover up now? Or is it that they're still unsuccessfully hiding the fact that their son is a worthless piece of shit? Speaking of which - why the hell do you want to go on a vacation with your ex and his fiancé?"

"Italy, Arya, it's Italy." Continuing on, Sansa's voice got quieter, almost a mumble. "And it's actually two exes. Harry's going."

"What?" Arya exclaimed. "Your old ex and your recent ex on the same trip. Why are you torturing yourself, Sansa? Is it really worth it?"

"Emphatically yes. I can't afford the type of vacation this is going to be. I can't miss out on it."

"Alright. You're going to go. Single. Thirty, flirty, and thriving, or whatever. You're going to do your best to ignore the twats and their judginess. And you'll more than likely meet some suave Italian man to spend some time with."

"First of all, I'm 28, not 30. Don't age me up, godsdammit." Sansa averted her eyes to the ground and began to mumble again as she trudged on. "And secondly, there's a small problem with that."

"What problem?" Arya asked, eyes narrowed.

"Well, I ran into Margaery today. She mentioned, in that annoyingly gossipy way of hers, that she had heard Harry and I broke up. And then she proceeded to inform me that Harry was still going to be coming on the trip and bringing along his new girlfriend."

"Wow, he's a dick. These people were more your friends - if you can call them that - than Harry's. He shouldn't be going on it now that you're not together. I bet it's to get back at you for breaking up with him. Maybe he thought it would get you to cancel on your dream vacation."

"Yeah, well, the problem came when Margaery started to get all condescendingly sympathetic, talking about how sorry she'll be to see me alone on the trip. So…I kinda told her I have a boyfriend now and that he'll be coming with me." Sansa rushed through that last part.

"You what? You lied and said you have a boyfriend? Why would you do that, idiot?"

"I don't know! She just made me so mad and frustrated with her fake pity, it just sort of slipped out of my mouth. And now I'm screwed. I either have to find one quickly or tell everyone I've lost another boyfriend in relatively quick succession, be considered a loser, and still be alone on the trip."

"When are you leaving?"

"In eight days."

"My gods, Sansa," Arya sighed, pinching the bridge of her nose. "Okay. Here's what we're going to do. We are going to list the men we know that could be your fake boyfriend."

"Fake boyfriend?"

"Yes. You started this by telling Margaery you have one. Now we have to find a real fake boyfriend. Give me something to write on," Arya commanded. Sansa hastily pulled out a notebook and pen from her desk, handing them over to her sister. Arya laid on the ground and started scrolling through her phone's contacts, directing Sansa to do the same, writing down the names she found as well as the ones Sansa spouted out. When they were done, Arya reviewed the list.

"It needs to be someone I can put up with for two weeks of travel," Sansa added.

"You cannot afford to be picky right now. Hmmmm. No. No. Eh, I don't think so," Arya said, going down the list. "Theon?"

"Oh gods, no. I love him, but I already can only put up with him for a day at a time. One or both of us wouldn't make it back home alive if I went with him. And I really don't think I can make a fake relationship with him believable. I can only see him like a brother."

"Again, can't be picky," Arya reminded her. "But now that I think of it, I very highly doubt he even has a passport. What about Sam?"

"While he would be pleasant and perfectly knowledgeable, he started dating Gilly, remember? I'm not gonna fake a relationship with someone who is in a legit one."

"Damn, that's right." Her sister continued to pore over the list. "Jon," she offered after a few moments of her eyes scanning the paper.

"Jon. Jon Snow? Are you kidding? I'm pretty sure he'd rather be dead than hang out with me and my friends with no escape for two weeks."

"He's single. I'm sure he can get out of work. He wouldn't take advantage of you in your fake relationship, unlike some of the other guys on this list. I trust him to keep you safe in a foreign country. And he would take no shit from your douche exes or the judgy brat-pack."

Sansa weighed her sister's reasons and her own options - or lack thereof. At least he's good looking and successful, she thought. "I still doubt he'd say yes."

"Doesn't hurt to ask," Arya shrugged. "Because, other than him, I think you're shit out of luck and going alone as the old spinster they think you are."

Sansa threw the pen at her sister for that.

Later that night, after she took all afternoon to plan out the words to ask Jon, Sansa laid in her bed with her phone clutched in her hand. She debated on calling or texting him. They didn't really have a calling-type of friendship, they rarely texted as it was.

Jon was super close to the whole Stark family, with the exception of herself. He was a neighborhood kid that Robb had basically adopted as a brother when they were little boys. Soon enough, both he and his mom were welcomed into the family with open arms. He was always around. He and Sansa got along through their years growing up, for the most part. There was some mutual teasing, but he was always kind to her. Which is more than she could say about herself. Sansa wasn't proud of it, especially now as she got older, but she tended to avoid him in high school, knowing her friends thought lowly of him. The Starks were very well off, but not nearly as wealthy as some of her friends. They all went to an exclusive prep school and Sansa yearned to fit in with the cool kids. Those cool kids frowned upon Jon's lack of wealth and his quiet demeanor; his only saving grace from being considered a total loser was that he was best friends with the ever-popular Robb. Her parents helped Jon's mom pay for his tuition so that he could get the same amazing education. It paid off. After high school, he went on to a great university and ended up with a masters. Now he worked in finance; Sansa didn't know any specifics of his job, thanks to the lack of closeness between them. She usually only saw him during family events and holidays. Jon had also written a novel, much to the surprise of everyone. It was published, released, and it was really gaining traction in popularity. Sansa bought and read it, just as the whole family did to support him. She didn't tell them she read it four times though. She found it so good and the mystery aspect was thrilling. But, above all, the beautiful romantic storyline shone brightly in the background of it. She secretly hoped he'd write another one.

It was getting late and she needed to make a decision. Before she could talk herself out of it, she pulled up his phone number and hastily pressed the call button. It rang and rang; the idea to just hang up tempted her. But before it could reach his voicemail, the ringing ceased.

"Hello?" Jon's unsure voice came through.

"Hi, Jon! It's Sansa!" She reminded herself to calm down and get rid of the nervous high pitched tone.

"Hey, how are you?"

Sansa could still hear the questioning in his voice as to why she was even calling him.

"I'm great! But I have a favor to ask of you."

"Go for it."

"Can you meet up at Castle Black Coffee tomorrow morning?" Sansa spit out. You idiot, you were supposed to just ask about the trip. Why are you dragging it out? she thought.

"Sure. Is - is that the favor?" Jon asked with a little laugh.

"Oh! No. I'll just go over it with you there. Is 9:30 okay?"

"Yup."

"Okay. See you there. Bye!" Sansa rushed and ended the call. She hung her head in her hands. Great. Stupid. Now you have to look him in the eye while basically professing what a loser you are that you need a fake boyfriend.

…

The next morning, Sansa walked into the coffee shop and found Jon just settling in at a table, coffee in hand. Sansa lamely waved and went to the counter to order her usual iced latte. Waiting for her drink at the pick up counter, she one again tried to find the words to start off this awkward conversation. After the barista called her name, she headed toward Jon, willing her nerves to calm down.

"Morning," he said simply with a curious look in his eye.

"Good morning!" Sansa squeaked before clearing her throat. "How are you?"

"I'm doing well. You?" he asked with a crooked smile.

"Great!" A moment's silence passed and Sansa let out a sigh. "You're obviously wondering why I've randomly asked you to grab coffee with me."

"I am intrigued, yes."

"Well. I needed to ask you a favor. First, do you have a valid passport?"

"Yes…"

"Would you be able to take off two weeks from work to go to Italy? With me."

"I'm sorry. What?" His face was a bit flabbergasted.

"Yeah. Italy. For two weeks. With me," Sansa repeated. "And a bunch of my old friends from King's Landing Prep," she added with a knowing grimace.

Jon's surprise look turned into a visible groan. "Two weeks with all of them?"

"Yeah," she said apologetically. "It's this whole 10 year reunion thing that we all made a promise to do when we were seniors. But, if it helps my cause, I should mention that we really only need to pay for our flights and food. All lodging, tours, and transportation within Italy is completely covered by the Baratheons."

"Baratheons? As in Joffrey Baratheon? Your awful ex is going on this trip? Who else is going?"

"Ellaria and her boyfriend. Daario and his girlfriend. Shae and her husband. Varys and his husband. Margaery."

"Isn't she engaged to Joffrey?"

Sansa plowed on. "Talisa and her husband."

"Robb's ex?"

"Viserys and his girlfriend."

"My ex's brother?"

"And Harry and his girlfriend."

"Another one of your exes? On the same trip? Sansa. Why do you even want to go?" Jon asked, leaning back in his chair with his eyes wide in disbelief.

"Ugh. You sound just like Arya. You probably don't remember, but I've always wanted to go to Italy. I had a phase in high school where I'm pretty sure I talked about it nonstop, trying to get my parents to send me there for a spring break one year. My dream of going there never stopped."

"Oh I remember. You had a whole dream board of Italy pictures in your room."

"I still have that dream board over the desk in my apartment, embarrassing as that is."

"It's not embarrassing, Sansa."

"Well, I've looked over the itinerary for this vacation and it's everything I could have wanted. Amazing 5 star hotels and magnificent villas, awesome tours that get you in everywhere. There's no way I could afford two weeks worth of that kind of stuff on top of the flight and daily incidentals."

"Alright, I can understand that," he offered, leaning forward. "And I can actually use this trip to my advantage. I'm sure I can get the time off, gods know I deserve it and I have yet to ask for more than a few days off in my years there. Mormont owes me a long vacation. I've been thinking about writing another book and setting it in Europe. I could easily settle for Italy. Maybe I could get some inspiration from the locales and learn some things."

Oooooh, he's writing another book! she excitedly thought. "That's great! But I should tell you that's not the entire favor I need to ask of you," Sansa added sheepishly.

"There's more? A partially paid trip to Italy isn't asking much of a favor, but having to go on it with that whole lot definitely is," Jon laughed.

"Um. Well," Sansa dropped her eyes down to her cup of coffee and fiddled with the straw. "I kinda need you to pretend you're my boyfriend." The silence was deafening. After a few moments, Sansa risked looking up at him. His face looked perplexed, brows knitted together and mouth partially fallen open. "I know. I'm so sorry to ask this of you. I ran into Margaery and she was just showering me in fake pity about my breakup with Harry, telling me he was still coming and bringing his girlfriend that he cheated on me with. It's like they all expected me to back out of the trip because of it. But fuck that. So I was stupid and confidently told her I'll be bringing my new boyfriend. Even though I don't have one. So now I'm an idiot and need to find a fake boyfriend. Or not show up with one and look like a loser. Or worse, not go."

"First of all, don't call yourself an idiot, you're not. What dates should I be asking off of work?"

"June 15th through July 1st," Sansa said with a cringe.

"This year? Sansa, that's in one week."

"I know. This is super last minute. I'm so sorry."

"Let me see what I can do. I'll let you know as soon as I find out about work."

"Thank you, Jon."

…

After work the next day, Sansa's phone rang. She looked at the screen, gasping as she found Jon's name and picture on it.

"Hi," she answered, her voice unsure and nervous.

"I was able to get off work," he stated.

"Oh my gods, that's amazing!"

"Yeah. But I have a problem. I have no idea what to pack or wear. I know all of your elitist friends can be overly critical about that sort of thing. We can't have your boyfriend stick out like a sore thumb."

Sansa laughed. She did recall them criticizing Jon's penchant for wearing a lot of grungy black clothing in school, something Sansa never really minded herself but she kept quiet about it to fit in. "I can help you. We need to book our flights, as well."

"Wanna come over? Kill two birds with one stone?"

"Leaving now."

It had been a while since she had been to Jon's place. Nervous butterflies filled her insides as she walked up to the door. This is so awkward. He opened to her knock with a crooked smile gracing his scruffy face.

"Thank you so much, Jon. You have no idea how grateful I am. I know it's completely silly for me to fake a whole relationship for people I generally do not care so much about anymore. But it's completely worth it to me."

"You're welcome, Sans. I could use the vacation anyway. Preferably it wouldn't be with the people I disliked in high school and who I thought I would never have to be around again. But at least I might get some good stuff going for my next book. Hopefully," Jon said, pulling out his laptop. "Book the tickets first?"

"Yes, sir."

Jon handed Sansa the laptop and she went to work finding the best flight that worked within the necessary time frame. Since they all had to pay for their own flights, the couples picked whatever worked best for them and were dispersed on different ones throughout the day. They'd check into the first hotel upon arrival, sleep and try to acclimate themselves to the local time zone, then the whole group would gather the next morning to start the trip. Since this was rather last minute, they didn't have many options. They ended up settling for a flight that left at night, having a layover in Switzerland, and landing in Italy the following night.

"First class?" Jon asked, looking over her shoulder as she went through the booking process.

"Jon, that is entirely way too much money!"

"I was just throwing it out there. What about business class? You don't want to look like a peasant in front of your friends, right?" Jon teased.

"Oh geez, I don't care about that. Normal 'peasant' seats work just fine for me."

"Hmmm. You've changed," he muttered, giving her an analyzing look.

"Yes, I have. I've grown up from the prissy, spoiled teen I once was. And I don't rely on my parents' money like so many of them do. And if any of those judgy bitches look down upon me for taking economy, so be it. Although, I would pay more for the extra legroom seats, which I see are miraculously available!"

"But you care what they think about you being single?"

"Okay, I have some kinks to work out. And I normally wouldn't care, but in this situation, I do."

Once their flights were booked, they headed to Jon's bedroom. Sansa had never been in it before and was somewhat surprised to find it neat and tidy. She sat down next to an empty suitcase on his bed.

"Are we going to do a movie fashion montage?" she asked with a teasing smile as he took out a stack of folded shirts from a drawer. He took one and threw it at her.

"Just tell me generally what kind of clothes to pack, punk."

Sansa laughed. "It sounds cheesy, but just be you."

"You don't care what they think about my appearance? I know none of them were very fond of me in the past, they didn't bother to hide their snobby looks from me."

"Nope. Don't care. You're already doing me the biggest favor, I'm not gonna attempt to turn you into one of those preppy boys. Bring attire that you'd feel comfortable walking around in. But throw in a few nice suits."

Over the next hour, Sansa helped Jon narrow down his selections. She had never really noticed before that his style had somewhat graduated to something that was a touch more sophisticated, in a Jon Snow type of way. She approved of the looks. Piles for different types of clothing were scattered about the bed.

"I think we did pretty good," Jon stated as they grabbed a couple slices of the pizza he had delivered to them.

"Me too," Sansa smiled. "Would you like to see the places I thought we could see when we're not doing group stuff?"

"Sure."

She pulled out a very worn notebook, the word "Italy" was decoratively written across the cover. "Now, I wrote a lot of the things in here a long time ago. None of this is set in stone; we can change anything if you have no interest in some of them or if you want to add anything to the list, I'll write it down."

"I'm sure your list is perfect. I know you've been trying to plan this for a long time. I trust your research."

Sansa smiled in relief.

…

The day of departure arrived. As planned, Jon met Sansa at her apartment after work. When she let him in, he found her a bit frazzled.

"Not everything is fitting in my bag," she fretted. "I put everything in here meticulously, in the best space-saving ways I know. But I still can't fit these shoes," she said, gesturing to a small pile of high heels.

Jon smirked. "And you need all those?"

"Yes." Her answer was decisive and sure.

"I'm going to look like garbage next to you," Jon softly laughed while rubbing at the back of his neck. "Here," he said, laying down his large suitcase and unzipping it. "I still have some room."

Sansa's eyes lit up and she gave a little squeal. Just as she finished situating her precious footwear in his suitcase, a car honked out front. "That would be Arya."

Arya drove them to LAX, merging into the usual Los Angeles traffic towards the busy airport. They finally arrived and unloaded the car. "Okay, you two lovebirds have fun!" Arya laughed as Sansa hugged her.

"Shut up, Arya," Sansa hissed.

"You take good care of my sister, Snow," she commanded when she hugged Jon.

"Yes, sir," he laughed.

"And bring me back a really good souvenir!" Arya shouted as they walked into the Thomas Bradley terminal.

Finding their airline, they checked in their luggage before carrying on to join the line for security check. They moved slowly through it until they were scanned and cleared. "Here, I'll carry your bag," Jon offered as he situated his backpack on his shoulders while Sansa put her shoes back on.

Already a better pseudo boyfriend than Harry was a real one, Sansa noted. "You sure? I think we have a bit of a walk to get to our gate."

"Of course." He picked up her weekender bag that perfectly matched her suitcase and they made their way out of the TSA area. Finding their gate, they headed over to a nearby wine bar. Sansa ordered a glass of wine to help ease her nerves about the flight. She didn't necessarily have a fear of flying. She was just a little scared during the take off. And landing. And whenever turbulence hit. But who wouldn't be?

When the charcuterie board they decided to share was placed between them, Sansa decided it was finally time to go over the awkward part - the groundwork for their faux relationship. "Okay. So, we should probably get on the same page with how we're gonna go about our situation," she proposed.

"Good idea. Can't just show up and not know what to do in front of them."

"We obviously don't need to be all lovey dovey 24/7," Sansa quickly said, not wanting Jon to feel uncomfortable around her. "Is hand holding every once in a while okay?"

"Sure. Arm around your shoulders?"

"Perfectly acceptable. Maybe sprinkle in an arm around my waist now and then. To mix things up."

"Noted."

"Maybe give me a compliment in front of them sometimes. And I'll do the same for you, of course."

"Would they expect us to kiss?"

That was the topic she was too nervous to broach herself. Not that she was repulsed by the thought. But she didn't want him to feel obligated to uncomfortably kiss someone he was raised with like a sister or something. "I do think it might be a little weird for a boyfriend and girlfriend to never be seen kissing in two whole weeks. But only if you're okay with that. You're already doing so much for me, I'm not gonna make you do things you really don't want to do."

"We can kiss a few times, sure."

The nervousness within her spread like wildfire. Calm down. "Alright. What about cute names?"

"Which do you find acceptable?"

"Harry called me 'sweetie'. I secretly hated it. How about just 'babe'?"

"Good. Simple. I request you call me 'stud muffin'," Jon said with a teasing smile.

"Absolutely not."

"Fine. Let's both just stick to 'babe'. Makes it easier."

"Now let's get our story straight. They obviously already know who you are. You aren't a stranger to them, which makes it a little harder I think."

"When did we start dating?"

"Well, it's been two months since I broke up with Harry. So let's split the difference and call it a month."

"Okay. And why did we decide to date after all these years of knowing each other?"

"I'm thinkin' we started to spend more time together and it kinda just clicked for both of us. So we gave it a shot and it's working so far."

"Straightforward but still vague. I like it."

"How are your acting skills?" Sansa asked.

"Um. I don't know, it's not like I've been in plays or anything," Jon laughed.

"I'm just wondering how believable you can make it. I think I'm pretty good. I honed my skills with acting like everything was perfect in both relationships with Joffrey and Harry. So I'm confident I can pull off this happier type of lie."

Once they were finished, they headed over to their gate and eventually boarded their flight. As the plane was taxiing to the runway, Sansa felt the nerves she typically got while flying come roaring back. When the plane revved up, preparing to take off down the runway, she automatically gripped the armrest.

"You okay?" Jon whispered, noticing her rigidity.

"Mmm hmm," she hummed with eyes closed tight as the plane picked up speed.

"Do you need to hold my hand?"

Sansa could feel the back of his hand brush against hers. She opened her eyes and saw his kind smile. He was always nicer than you deserved, she thought.

"We could use the practice," he joked. It got her to crack a smile and she released her death grip on the armrest and slid it into Jon's hand. Her tight grip made him smile through a slight grimace he tried to hide.

"Thanks," she whispered as she let go when the plane leveled out high above Los Angeles.